Mandelic acid ester of n-methylpiperidinol-4



Patented Feb. 20, 1945 2376A MANDELIC ACID ESTER OF N-METHYL- PIPERIDINOL-4 Carl J. Klemme, Bronxville, and Richard Baltzly, New York, N. Y., assignors to Burroughs Wellcome & Co. (U. S. A.) Inc., New York, N. Y., a corporation of New York No Drawing. Application January 29, 1943, Serial No. 473,960

1 Claim. (Cl. 260-294) This invention relates t a mydriatic which is be reacted in dilute acid solution. The solution useful as a substitute for homatropine or its salts may then be alkalized and extracted with a waand to a method of making the same. ter immiscible solvent. The solution may be re- An object is to provide a novel and improved acted with a soluble acid to form the desired salt substance of the above type and a method of 5 of the above ester. After purification the base making the same from readily available subcan be isolated. stances. Various salts of N-methylpiperidinol-4 may be Other objects and advantages will be apparent used in preparing the material such as the hydroas the nature of the invention is more fully chloride, sulphate, phosphate, oxyl e, rtr te,

disclosed. malate, succinate, etc. The corresponding salt In accordance with the present invention we of the ester may be used or the base may be obhave found that the mandelic acid ester of N- tained therefrom.

methylpiperidinol-a and its salts having the As a specific example N-methylpiperidinol-4 formula hydrochloride and mandelic acid may be reacted in warm 10% hydrochloric acid for a sufficient O r time to form the ester. The solution may then CHsN CHO.C.CHOH.C5H5.HX be diluted with water and extracted with ether to recover mandelic acid. The aqueous layer may CHr-CHB be made alkaline with sodium carbonate and expossesses desirable mydriatic properties and is tracted repeatedly with ether. The ethereal so-.

suitable for use as a substitute for homatropine or lution may be dried over potassium carbonate and its salts. treated with gaseous hydrogen chloride, to pre- This ester may be prepared by esterifying N- cipitate the hydrochloride of the base as a syrup methylpiperidinol-4 with mandelic acid. as folwhich may be crystallized from aqueous acetone lows: and ether.

A specific example has been given only as an CHFCHZ illustration. Modifications may be made a will GESN shone-13000030130635 be apparent to a person skilled in the art.

What is claimed is: A compound selected from the group consist- E ing of the mandelic acid ester of N-mcthyl- CHSN CHO.C.OHOH.C@H5 piperidinol-4 and its salts prepared for use as a GHzwOH2 mydriatic.

, CARL J. KLEMME. N-methylpiperidinol-4 and mandelic acid may RICHARD B LTZLY. 

